Synthesis, Crystal Structure and Spectroscopic Properties of 1,2-Benzothiazine Derivatives: An Experimental and DFT Study" />
Synthesis, Crystal Structure and Spectroscopic Properties of 1,2-Benzothiazine Derivatives: An Experimental and DFT Study" />
1,2-benzothiazine,B3LYP/6-31+G(d),density functional theory (DFT),HUMO-LUMO,cyrstal structure,"/>
<div style="line-height: 150%">Synthesis, Crystal Structure and Spectroscopic Properties of 1,2-Benzothiazine Derivatives: An Experimental and DFT Study</div>
1,2-Benzothiazine derivatives methyl 3-methoxy-4-oxo-3,4-dihydro-2H-benzo[e] [1,2]thiazine-3-carboxylate 1,1-dioxide (1) and methyl 2-ethyl-3-hydroxy-4-oxo-3,4-dihydro-2H-benzo[e][1,2]thiazine-3-carboxylate 1,1-dioxide (2) were synthesized, and characterized by spectroscopic techniques; 1H-NMR and infrared (IR) spectroscopy. Crystals of 1 and 2 were grown by slow evaporation of methanol and ethyl acetate, respectively and their crystal structures were investigated by single-crystal X-ray diffraction analysis. Geometric properties were calculated by the B3LYP method of density functional theory (DFT) at the 6-31G+(d) basis set to compare with the experimental data. Simulated properties were found in strong agreement with the experimental ones. Intermolecular forces have also been modeled in order to investigate the strength of packing and strong hydrogen bonding was observed in both compounds 1 and 2. Electronic properties such as Ionization Potential (IP), Electron Affinities (EA) and coefficients of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) of compounds 1 and 2 were simulated for the first time.
1,2-Benzothiazine derivatives methyl 3-methoxy-4-oxo-3,4-dihydro-2H-benzo[e] [1,2]thiazine-3-carboxylate 1,1-dioxide (1) and methyl 2-ethyl-3-hydroxy-4-oxo-3,4-dihydro-2H-benzo[e][1,2]thiazine-3-carboxylate 1,1-dioxide (2) were synthesized, and characterized by spectroscopic techniques; 1H-NMR and infrared (IR) spectroscopy. Crystals of 1 and 2 were grown by slow evaporation of methanol and ethyl acetate, respectively and their crystal structures were investigated by single-crystal X-ray diffraction analysis. Geometric properties were calculated by the B3LYP method of density functional theory (DFT) at the 6-31G+(d) basis set to compare with the experimental data. Simulated properties were found in strong agreement with the experimental ones. Intermolecular forces have also been modeled in order to investigate the strength of packing and strong hydrogen bonding was observed in both compounds 1 and 2. Electronic properties such as Ionization Potential (IP), Electron Affinities (EA) and coefficients of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) of compounds 1 and 2 were simulated for the first time.
This project was funded by the Saudi Basic Industries Corporation (SABIC) and the Deanship of Scientific Research (DSR), King Abdulaziz University, Jeddah, under grant no. (MS/15/396/1434)
The authors, therefore, acknowledge with thanks SABIC and DSR technical and financial support
通讯作者:
E-mail: mnachemist@hotmail.com and mnarshad@kau.edu.sa for MUHAMMAD Nadeem Arshad,
and mahmood@ciit.net.pk for TARIQ Mahmood
E-mail: mahmood@ciit.net.pk
引用本文:
.
Synthesis, Crystal Structure and Spectroscopic Properties of 1,2-Benzothiazine Derivatives: An Experimental and DFT Study
[J]. 结构化学, 2015, 34(1): 15-25.
MUHAMMAD Nadeem Arshad;TARIQ Mahmood;ATHER Faroque Khan;MUHAMMAD Zia-Ur-Rehman;ABDULLAH M. Asiri;ISLAM Ullah Khan;RIFFAT-Un-Nisa;KHURSHID Ayub;AZAM Mukhtar;MUHAMMAD Tariq Saeed.
Synthesis, Crystal Structure and Spectroscopic Properties of 1,2-Benzothiazine Derivatives: An Experimental and DFT Study
. CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2015, 34(1): 15-25.
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